Medical hardships are common in the United States due to rising medical expenditures and patient-financial responsibilities. Meanwhile, every year, billions of dollars are lost to penalties from early withdrawals from retirement accounts to pay for these medical bills. Prior research has been devoted to the interrelation between the medical hardships and medical affordability. Separately, attention has been paid to the leakage impact of the early withdrawals from retirement withdrawals. This study explores the linkage between medical hardships and early withdrawals from retirement accounts. We ask whether the medical hardships, such as unpaid medical debt, unfilled prescriptions due to cost, and medical-care avoidance due to cost, are associated with early withdrawals from retirement accounts. We then discuss the negative financial impact of early withdrawals from retirement accounts on retirement readiness. Lastly, we explore the potential impact of the vicious circle among the low-income, uninsured, medical hardship sufferers coupling to their early withdrawals from retirement accounts and retirement readiness.